Dicarboxylic acid oxidation products

Abstract

What is disclosed is a dicarboxylic acid oxidation product of a immunologically reactive mono- or a polysaccharide having vicinal diols.

We claim: 
     
       1. A method of making a chemical compound that is a dicarboxylic acid oxidation product of an immunologically reactive mono- or a polysaccharide having vicinal diols, comprising the steps of: (a) providing a mono- or a polysaccharide having a group capable of specific binding with an immunologically reactive analyte (ligand) and two vicinal diols located on a terminal saccharide group; and   (b) oxidizing said terminal saccharide at the vicinal diol portion with a mixture of periodic acid and chromium trioxide in aqueous mixture containing a miscible organic solvent to produce the dicarboxylic acid oxidation product.   
     
     
       2. The method of claim 1 wherein the dicarboxylic acid oxidation product represented by the structure: ##STR5## wherein; R is an immunologically reactive group devoid of vicinal diol, carboxylic acid, primary amine and sulfhydryl groups; Z represents the residual atoms of a saccharide group having dicarboxylic acid groups formed from the oxidation of the carbon atoms containing vicinal diol groups;   Z' represents the atoms necessary to complete a saccharide group; and   n is an integer from 0 to about 2,500.   
     
     
       3. The method of claim 2 wherein the dicarboxylic acid oxidation product has the structure: ##STR6## wherein; R is an immunologically reactive group devoid of vicinal diol, carboxylic acid, primary amine and sulfhydryl groups; R 1 , each independently, represents hydrogen, lower alkyl, lower alkoxy, lower alkanamido, hydroxy or hydroxymethyl, in which "lower" refers to carbon chains of about 1 to 4 carbon atoms;   the linkages between monosaccharide units is an α or β glycosidic bond; and   n is an integer from 0 to about 2,500.   
     
     
       4. The method of claim 3 wherein R is a steroid group. 
     
     
       5. The method of claim 4 wherein the steroid group is selected from the group consisting of digoxin, digitoxin or ouabain. 
     
     
       6. The method of claims 1, 2, 3, 4 or 5 wherein the mixture of periodic acid and chromium dioxide has a molar concentration ratio in the range of 4/1 to 1/1. 
     
     
       7. The method of claim 6 wherein the ratio is 2/1. 
     
     
       8. The method of claim 7 wherein the water miscible organic solvent is selected from the group consisting of dioxane, methanol, ethanol, propanol, isopropanol, DMF and acetone.